In Defense of Jesse Winchester

With the news that the singer-songwriter has passed, it's time to look back on someone Bob Dylan once dubbed 'The Greatest Living Songwriter'.

“That’s it, Jesse. The show’s over. You finished me off. It happened at rehearsals and it happened now.”

Such was sheepishly uttered from the great Elvis Costello during an episode of the short-lived television series Spectacle. The Jesse in that sentence refers to Jesse Winchester, who had just finished performing his new song, “Sham-A-Ling-Dong-Ding”. He ran through it all by himself as Costello, the show’s host, Sheryl Crow, Ron Sexsmith and Neko Case sat silently next to him on stage. As the performance neared its conclusion, the camera focused in on Case, who was crying. Costello, as the top quote illustrates, did his best not to join her, even if those glasses of his appeared to be filling with mist. 

Anybody with a working heartbeat could see why. Accompanied by a lightly plucked acoustic guitar, the singer’s humbled, weightless voice begins:

The boys were singing shing-a-ling

The summer night we met

You were tan and seventeen

O, how could I forget

When every star from near and far

Was watching from above

Watching two teenagers fall in love

The mere words, while pitch-perfect, don’t do the performance at hand justice. Instead, it’s the dichotomy of the songwriter’s stern demeanor coupled with a presentation doused with humility that makes those four minutes feel as though time ceased to move forward. The whole thing is transfixing in an eerie, vulnerable way, like you want to give him a hug, even if you know he might not hug you back. And it wouldn’t be because he couldn’t use one; rather, something about his body language says he feels as though he simply doesn’t deserve one. 

Or, as Janis Ian wrote when initial reports of Winchester’s death surfaced, “As underrated a singer as Chet Baker. As underrated a guitarist as Willie Nelson. A man who held the audience in the palm of his hand without moving an inch. One of the best songwriters on earth. Damn damn damn.” (“Tribute: Jesse Winchester”, LVVN Music, 7 April 2014)

I had never heard the name Winchester until I saw that performance. Shame on me. If there are to be such things as angels and Heaven, I’d be awfully surprised to find out they didn’t have that voice of his sound-tracking everything they do. It possesses an inherent ability to pacify, even if such was never his intention. Watching feathers drop from a pillow wouldn’t be nearly as soft as the guy’s vocal tones sound. You could fall asleep in them, even if you just awoke from a full night’s sleep. 

Maybe that’s why, when I saw a smattering of Twitter messages reporting his death, false or not, I could hardly bring myself to Google the news, in fear that the speculative whispers might be too loud and too true to digest. In fact, even as I write now, I have no idea where his health might stand by the time this column publishes. All I really know is that he is (or was) gravely ill, and should he be lucky enough to squeeze out a few more days, weeks or months, the prognosis isn’t good. One way or the other, that brilliantly observant mind and those plaintively perfect vocal sounds have little room for further practice. If the world hasn’t been robbed of them by the time you read this, all signs point that their fate is coming much sooner than later. 

And perhaps it’s a little poetic that it end this way: One shot of sadness followed by a string of grief, conflicting reports, and a lingering flirtation with disaster. After all, Winchester’s was a career that embodied melancholy, almost front to back. Born on 16 May 1944, the singer moved to Montreal after he graduated from Williams College in Massachusetts and received his draft notice. Rather than be shipped off to fight in the Vietnam War, he headed North and refused to look back even in 1976, when Jimmy Carter granted amnesty to those who evaded the draft. Though Winchester performed in Vermont in 1977, he wouldn’t move back to the States for good until 2002. 

This would ultimately paint the colors that made up his life, despite his insistence through the years that he never had much interest in penning political songs. “It’s possible I got more notoriety from my political life than I would have gotten from my musical life,” The Toronto Star quoted him as saying in a story it published last week. “It’s just impossible to know.” (“Jesse Winchester clinging to life, despite reports of his death: family”, by Peter Edwards, 7 April 2012)

It’s also impossible to know how far his career would have taken him, had he enjoyed just a little more exposure stateside. Bob Dylan once famously said of the singer, “You can’t talk about the best songwriters and not include him.” Throngs of people saw a trajectory similar to that of James Taylor in Winchester’s work. And Rolling Stone said he had “the greatest voice of the decade” in the ’70s. Yet for all the accolades and compliments, his popularity was stifled — as well as, sadly, overshadowed — by his resistance to war, by his move to Canada during one of the most contentious, polarizing eras in American history. 

That didn’t stop his peers from recognizing his gifts, at least. In 2012, Mailboat Records released Quiet About It, a de facto tribute album that featured everyone from Rosanne Cash, to Allen Toussaint, to Vince Gill, to Lyle Lovett, to the aforementioned Costello performing their favorite Winchester songs. In all his humor and earnest, the songwriter addressed it on his blog:

When I was sick last year, fixing to die, some friends decided to make a CD of various artists performing my songs. Jimmy Buffett wrote me around Christmastime with the news. I struggled out of my chair and did a little boogaloo around the living room. I guess I wasn’t that sick,” he wrote before eventually adding in regards to his concert schedule, “here’s a page where you can exchange your cumbersome money for priceless, practically weightless music.” (“Jesse Winchester’s Studio”)

See. He knew how to laugh, too. 

Actually, that self-deprecating ingredient to the gourmet meal that is Winchester is a taste essential to his appeal. “Poet” isn’t a word I particularly like to throw around, but there are very few other people in this world more deserving of such a categorization. There was something that separated him from his contemporaries, an amount of levity, an amount of intellect that brought his tales of heartbreak, innocence, youth and romance to life.

There was no whining with him, no sense of entitlement. He understood that ever-elusive “It” that so many of us fail to oftentimes grasp. His combination of acceptance and acumen proved to listeners that he wasn’t just singing for himself; he was singing for anyone who’s ever had to find comfort within the fabric of life’s most uncomfortable moments. 

He simply knew how to weave words together in ways most people only wished they could. Throw that on top of his woebegone voice and you suddenly realize the connection he creates with his art is far more visceral than passive, far more rooted than universal. Check out how bitingly affective this tiny passage from “The Brand New Tennessee Waltz” is:

When I leave it will be like I found you love

Descending Victorian stairs

And I’m feeling like one of your photographs, girl

Trapped while I’m putting on airs

Getting even by saying, ‘Who cares’

Now, that is hurt. That is pain. That can’t be written without experience. That doesn’t happen if you fail to possess a certain perspective, a certain ability. That is why Winchester matters. And that, friends, is why the news of his flailing health continues to be heartbreaking, continues to examine the presence of luck, and continues to dispute the always-contested precept of fairness that blesses some people and curses others. 

“I don’t know anyone who dislikes Jesse Winchester’s music,” Bill Flanagan wrote in the liner notes to Quiet About It. “It seems to me that there are only those who love it and those who have never heard it. Jesse is a songwriter’s songwriter, praised by every composer from Dylan down and covered by greats from Wilson Pickett to the Everly Brothers. Jesse Winchester’s songs are like mirrors in which both performers and listeners can see themselves… This album is a tribute to a great singer/songwriter and also to the community of musicians who pulled together to show their love and respect to Jesse when he was down. Now that Jesse is back up, make sure you see him when he comes to your town. They are not making any more like him.” (“Jesse Winchester”, Mail Boat Records)

A couple years ago — not too long after I first came across that Spectacle performance, in fact — I noticed that Winchester was set to perform in the area. Because it was on a day of the week that was easy for me and because it was close, I toyed with the idea of picking up a ticket. Ultimately, I didn’t go. Other plans crept up, or I didn’t feel like spending the money, or I had work that needed to get gone, or something unforeseen happened. 

Upon first reading the news of his health last weekend, I almost instantly flashed to that missed opportunity. Something about the scenario seemed ironic to me in a personal sense, be it the through-line of forgotten chances that wove its way through Winchester’s career as a musician, or the mere fact that by the time I finally found out who this guy was, it was almost too late to see him in person. I’ll catch him the next time around, I remember thinking. I was wrong, of course. A next time will never happen. 

But that doesn’t mean we aren’t left with a hell of a catalogue to digest. It doesn’t mean that the singer will soon be forgotten, even if that supremely curious voice is now singing at the one place it was always supposed to sing anyway: Among angels. “I’m certainly not a hero,” Winchester once told someone who tried to suggest otherwise. “I’m not sure what I am, but I know for sure I’m not a hero.”

Maybe. But, even if his humble ways wouldn’t let him admit it, it’s tough to imagine that Winchester doesn’t know that there’s something tremendously heroic about creating an art so profound it can bring one to tears. Because, to borrow a little from one of the last poets himself…

As every word in his sweet old love songs 

continues to ring true 

Sham-a-ling-dong-ding means timeless

And the voice of Jesse Winchester does, too.

Splash image: Press photo. Photographer unknown.